WO2005053844A1 - Procede de production d'un catalyseur destine a la production d'aldehyde insature et d'acide carboxylique insature - Google Patents

Procede de production d'un catalyseur destine a la production d'aldehyde insature et d'acide carboxylique insature Download PDF

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Publication number
WO2005053844A1
WO2005053844A1 PCT/JP2004/013459 JP2004013459W WO2005053844A1 WO 2005053844 A1 WO2005053844 A1 WO 2005053844A1 JP 2004013459 W JP2004013459 W JP 2004013459W WO 2005053844 A1 WO2005053844 A1 WO 2005053844A1
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Prior art keywords
catalyst
producing
unsaturated carboxylic
unsaturated
carboxylic acid
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PCT/JP2004/013459
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English (en)
Japanese (ja)
Inventor
Isao Teshigahara
Nariyasu Kanuka
Kazuharu Tazawa
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Mitsubishi Chemical Corporation
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Priority to US11/033,131 priority Critical patent/US7279442B2/en
Publication of WO2005053844A1 publication Critical patent/WO2005053844A1/fr

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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
    • C07C45/27—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation
    • C07C45/32—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation with molecular oxygen
    • C07C45/33—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation with molecular oxygen of CHx-moieties
    • C07C45/34—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation with molecular oxygen of CHx-moieties in unsaturated compounds
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J23/00—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00
    • B01J23/002—Mixed oxides other than spinels, e.g. perovskite
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J23/00—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00
    • B01J23/70—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of the iron group metals or copper
    • B01J23/76—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of the iron group metals or copper combined with metals, oxides or hydroxides provided for in groups B01J23/02 - B01J23/36
    • B01J23/84—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of the iron group metals or copper combined with metals, oxides or hydroxides provided for in groups B01J23/02 - B01J23/36 with arsenic, antimony, bismuth, vanadium, niobium, tantalum, polonium, chromium, molybdenum, tungsten, manganese, technetium or rhenium
    • B01J23/85—Chromium, molybdenum or tungsten
    • B01J23/88—Molybdenum
    • B01J23/887—Molybdenum containing in addition other metals, oxides or hydroxides provided for in groups B01J23/02 - B01J23/36
    • B01J23/8876—Arsenic, antimony or bismuth
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J37/00—Processes, in general, for preparing catalysts; Processes, in general, for activation of catalysts
    • B01J37/0009—Use of binding agents; Moulding; Pressing; Powdering; Granulating; Addition of materials ameliorating the mechanical properties of the product catalyst
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J37/00—Processes, in general, for preparing catalysts; Processes, in general, for activation of catalysts
    • B01J37/0009—Use of binding agents; Moulding; Pressing; Powdering; Granulating; Addition of materials ameliorating the mechanical properties of the product catalyst
    • B01J37/0027—Powdering
    • B01J37/0045—Drying a slurry, e.g. spray drying
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
    • C07C45/27—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation
    • C07C45/32—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation with molecular oxygen
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
    • C07C45/27—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation
    • C07C45/32—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation with molecular oxygen
    • C07C45/33—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation with molecular oxygen of CHx-moieties
    • C07C45/34—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation with molecular oxygen of CHx-moieties in unsaturated compounds
    • C07C45/35—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation with molecular oxygen of CHx-moieties in unsaturated compounds in propene or isobutene
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
    • C07C45/27—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation
    • C07C45/32—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation with molecular oxygen
    • C07C45/37—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation with molecular oxygen of >C—O—functional groups to >C=O groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
    • C07C51/16—Preparation of carboxylic acids or their salts, halides or anhydrides by oxidation
    • C07C51/21—Preparation of carboxylic acids or their salts, halides or anhydrides by oxidation with molecular oxygen
    • C07C51/25—Preparation of carboxylic acids or their salts, halides or anhydrides by oxidation with molecular oxygen of unsaturated compounds containing no six-membered aromatic ring
    • C07C51/252—Preparation of carboxylic acids or their salts, halides or anhydrides by oxidation with molecular oxygen of unsaturated compounds containing no six-membered aromatic ring of propene, butenes, acrolein or methacrolein
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J2523/00—Constitutive chemical elements of heterogeneous catalysts
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J35/00—Catalysts, in general, characterised by their form or physical properties
    • B01J35/30—Catalysts, in general, characterised by their form or physical properties characterised by their physical properties
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J37/00—Processes, in general, for preparing catalysts; Processes, in general, for activation of catalysts
    • B01J37/0009—Use of binding agents; Moulding; Pressing; Powdering; Granulating; Addition of materials ameliorating the mechanical properties of the product catalyst
    • B01J37/0027—Powdering
    • B01J37/0036—Grinding
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J37/00—Processes, in general, for preparing catalysts; Processes, in general, for activation of catalysts
    • B01J37/02—Impregnation, coating or precipitation
    • B01J37/0236—Drying, e.g. preparing a suspension, adding a soluble salt and drying

Definitions

  • the present invention relates to a method for producing a catalyst for producing unsaturated aldehydes and unsaturated carboxylic acids.
  • the present invention provides a method for producing the corresponding unsaturated aldehyde and unsaturated carboxylic acid by gas-phase catalytic oxidation of olefin, tertiary butyl alcohol, or methyl tertiary butyl ether with a molecular oxygen-containing gas.
  • the present invention relates to a method for producing a catalyst which has high mechanical strength, is stable over a long period of time, and can produce the corresponding unsaturated aldehyde and unsaturated carboxylic acid in high yield.
  • Patent Literature 1 Patent Literature 2, Patent Literature 3, and the like are known as such examples.
  • This method has the advantage that the pore size of the catalyst can be changed relatively freely by adding an organic compound having a different type or particle size during the production of the catalyst and removing the used organic compound by heat treatment.
  • this method when the organic compound is removed, sintering of the catalyst by combustion of the organic compound and reduction of the catalyst by the organic compound occur, so that the activation treatment is complicated and the catalyst performance is reduced. There is a problem of lack of reproducibility of.
  • Patent Document 4 discloses that activated carbon is used during the production of the catalyst. That is, a mixture of the above-mentioned catalyst components is calcined, the obtained calcined product is mixed with activated carbon having a predetermined particle size, shaped, and heat-treated. However, also in this case, there is room for further improvement in the yield of the desired unsaturated aldehyde and unsaturated carboxylic acid.
  • Patent Document 1 Japanese Patent Application Laid-Open No. 58-98143
  • Patent Document 2 Japanese Patent Publication No. 3-109946
  • Patent Document 3 Japanese Patent No. 3278246
  • Patent Document 4 Patent No. 3251641
  • an object of the present invention is to respond to each of olefin, tertiary butyl alcohol, or methyl tertiary butyl ether by gas phase contact oxidation with a molecular oxygen-containing gas.
  • Another object of the present invention is to provide a method for producing a catalyst which can produce unsaturated aldehydes and unsaturated carboxylic acids in a high yield with good reproducibility and has high mechanical strength and high durability.
  • the present inventors have conducted intensive studies to solve the above-mentioned problems, and found that a composite oxide catalyst containing at least molybdenum, bismuth, and iron for producing unsaturated aldehydes and unsaturated carboxylic acids.
  • a composite oxide catalyst containing at least molybdenum, bismuth, and iron for producing unsaturated aldehydes and unsaturated carboxylic acids.
  • the amount of water contained in a mixed solution containing a catalyst component or a dried product of a slurry thereof is 0.3 to 4% by weight. %.
  • the desired unsaturated aldehyde and unsaturated carboxylic acid can be produced with high yield and reproducibility, and a molded catalyst having high mechanical strength and stability can be obtained.
  • the moisture content of the above dried product is less than 0.3% by weight, the molding pressure required to obtain good properties increases, and catalyst molding with stable properties is performed. I can't get my body.
  • the characteristics of the catalyst are changed by the calcination step following the molding, and a molded catalyst having stable characteristics cannot be obtained.
  • the present invention is characterized by the following constitution.
  • a method for producing a composite oxide catalyst containing at least molybdenum, bismuth, and iron comprising drying a mixed solution or an aqueous slurry containing the above-mentioned catalyst components to obtain a dried product having a water content of 0.3-4.
  • a method for producing a catalyst for producing unsaturated aldehydes and unsaturated carboxylic acids wherein the catalyst is adjusted to a weight percent and tablet-molded to form a molded product.
  • the molded body has an outer diameter of 3-10 mm, an inner diameter of 0.1-0.7 times the outer diameter, a length of 0.5-12 times the outer diameter, and is open in the length direction.
  • X is at least one element selected from the group consisting of Na, K, Rb, Cs, and T1
  • Y is at least one element selected from the group consisting of B, P, As, and W
  • Z is at least one element selected from the group consisting of Mg, Ca, Zn, Ce and Sm
  • Q is halogen
  • a to k represent the atomic ratio of each element.
  • the mixed solution containing the catalyst component or the slurry thereof is dried and molded.
  • a new idea based on a new concept of controlling the amount of moisture contained in the dried product to a specific range and compressing it into tablets has a high mechanical strength, is stable for a long time, and has a high yield.
  • the present invention provides a catalyst capable of producing the corresponding unsaturated aldehyde and unsaturated carboxylic acid by gas-phase catalytic oxidation of olefin, olefin, tertiary butyl alcohol, or methyl tertiary butyl ether with a molecular oxygen-containing gas.
  • the catalyst produced in the present invention is obtained by subjecting olefin, tertiary butyl alcohol, or methyl tertiary butyl ether to gas-phase catalytic oxidation with a molecular oxygen-containing gas in the gas-phase catalytic oxidation, respectively.
  • a catalyst for producing an acid which is a composite oxide catalyst containing at least molybdenum, bismuth, and iron.
  • the present invention can be applied to any catalyst as long as it is a composite oxide catalyst containing such three components. Among them, a catalyst represented by the following formula (1) is particularly preferable.
  • Mo molybdenum
  • Bi bismuth
  • Co cobalt
  • Ni nickel
  • Fe iron
  • Si silicon
  • O oxygen
  • X, Y, Z, Q, a—k, and k are as defined above.
  • the starting compound containing each elemental component of the catalyst is appropriately dissolved or dispersed in an aqueous medium in a required amount according to the composition of the catalyst to be produced, whereby the catalyst is prepared.
  • a mixed solution containing the components or an aqueous slurry thereof is produced.
  • a nitrate, an ammonium salt, a hydroxide, an oxide, a sulfate, a carbonate, a halide, an acetate, or the like containing each element is used.
  • molybdenum ammonium paramolybdate, molybdenum trioxide, molybdenum chloride and the like are used.
  • a non-aqueous solvent such as alcohol can be added to the aqueous medium as needed to adjust the viscosity.
  • the mixed solution or the aqueous slurry containing the catalyst component is preferably sufficiently stirred and mixed in order to prevent uneven distribution of each component.
  • the mixed solution or the aqueous slurry containing the catalyst component is dried, and the drying can be performed by various methods.
  • a powdery dried product may be obtained using a usual spray dryer, slurry dryer, drum dryer or the like, but drying with a spray dryer is particularly preferred.
  • the water content of the dried product is 0%. 3-4% by weight.
  • the moisture content of the dried product is defined as in equation (2).
  • W1 is the weight when the dried product is evaporated to dryness at 150 ° C for 10 hours
  • W2 is the weight of the dried product.
  • Water content (W2-WD / W1 ⁇ 100 )
  • a mixed solution or an aqueous slurry containing a catalyst component is used as a method of controlling the water content of the dried product subjected to molding to the above range.
  • the drying may be performed under controlled conditions, or may be performed by subjecting the manufactured dried product to appropriate humidification by, for example, spraying moisture. It is necessary to control the moisture content of the dried product within the above range, and in the present invention, the moisture content of the dried product is preferably 0.4 to 3% by weight.
  • the shape of the molded product may be any of a spherical shape, a cylindrical shape, a ring shape, and the like, and various sizes can be appropriately selected.
  • the molded body is ring-shaped, the outer diameter is 3 to 10 mm, the inner diameter is 0.1 to 0.7 times the outer diameter, and the length (height) is 0.1 mm of the outer diameter. It is 5-2 times, and is open in the length (height) direction, and a round shape is preferable because of a point force such as a small pressure loss.
  • inorganic fibers such as glass fibers and various whiskers may be used in order to improve the mechanical strength and the degree of powdering of the molded product.
  • additives commonly known as a binder such as ammonium nitrate, cellulose, starch, polyvinyl alcohol, and stearic acid can be used.
  • the dried molded article containing the catalyst component obtained as described above is subsequently calcined.
  • the calcination is carried out in the presence of an oxygen-containing gas, preferably at 400 to 650 ° C, particularly preferably at 450 to 600 ° C, preferably for 1 to 15 hours, particularly preferably for 3 to 12 hours.
  • an atmosphere firing furnace can be used.
  • the atmosphere firing furnace for example, a method in which a fixed bed reactor is filled with a catalyst and heated externally under the flow of an atmosphere gas, a method in which the fixed bed reactor is of a heat exchange type, an atmosphere gas inside a Matsufuru furnace is used.
  • a method of circulating the gas, a method of circulating the atmosphere gas inside the tunnel furnace, a method of circulating the atmosphere gas inside the kiln furnace, and the like can be used.
  • a fixed bed reactor is filled with a catalyst and heated externally under the flow of atmosphere gas, and more preferably, the catalyst is placed in a heat exchange fixed bed reactor. And heating from the outside while the atmosphere gas is flowing.
  • the atmospheric gas besides air, a mixed gas of air and an inert gas such as nitrogen can be used. Air can be preferably used because it is economically advantageous.
  • olefin, tertiary butyl alcohol, or methyl tertiary butyl ether is subjected to gas-phase catalytic oxidation with a molecular oxygen-containing gas, and the corresponding unsaturated aldehyde and
  • the method for producing an unsaturated carboxylic acid can be carried out by an existing method.
  • the reaction is performed using a fixed-bed tube reactor.
  • the reaction can be carried out by a simple flow method or a recycling method through the reactor. Under the conditions generally used for the reaction of
  • a mixed gas such as propylene (11-15% by volume), molecular oxygen (3 to 30% by volume), steam (0 to 60% by volume), and an inert gas such as nitrogen and carbon dioxide (20 to 80% by volume) is used.
  • the catalyst is introduced into the catalyst layer filled in each reaction tube having an inner diameter of preferably 15 to 50 mm at 250 to 450 ° C. under a pressure of 0.1 to 1 MPa and a space velocity (SV) of 300 to 5000 hr- 1 .
  • SV space velocity
  • Pure water was added to the obtained granular solid and wet-pulverized, and the obtained slurry was dried with a spray drier at an inlet temperature of 300 ° C and an outlet temperature of 125 ° C.
  • the water content of the obtained dried product was measured and found to be 1.5% by weight.
  • the tablet molded product was placed in a firing container, and fired at 510 ° C. for 4 hours while flowing a small amount of air to produce a composite oxide catalyst.
  • the catalyst calculated from the charged raw materials is a composite oxide having the following atomic ratio.
  • Mo: Bi: Co: Ni: Fe: Na: B: K: Si 12: l: 4: 2: l: 0.1: 0.2: 0.1: 15
  • the drop strength of this catalyst was measured, it was 98.5%. there were.
  • a catalyst was prepared in the same manner as in Example 1 except that the outlet temperature of the spray dryer was set at 160 ° C. The water content of the dried product was 0.2% by weight. The measured drop strength of the catalyst was 90.1%.
  • a catalyst was prepared in the same manner as in Example 1 except that the outlet temperature of the spray dryer was set at 95 ° C.
  • the water content of the obtained dried product was 5.0% by weight.
  • the measured drop strength of the catalyst was 91.5%.
  • the catalyst produced by the method of the present invention is obtained by subjecting olefin, tertiary butyl alcohol, or methyl tertiary butyl ether to gas-phase catalytic oxidation with a molecular oxygen-containing gas to obtain the corresponding unsaturated aldehyde and Used to produce unsaturated carboxylic acids.
  • the unsaturated aldehydes and unsaturated carboxylic acids produced are widely used as raw materials for various chemicals, monomers for general-purpose resins, monomers for functional resins such as water-absorbing resins, flocculants, and thickeners. Used for applications.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Catalysts (AREA)

Abstract

L'invention concerne un nouveau procédé de production d'un catalyseur qui possède une résistance mécanique élevée et qui permet de produire de manière stable, avec un bon rendement sur une longue durée, un aldéhyde insaturé et un acide carboxylique insaturé correspondants. Le procédé précité permet de produire un catalyseur qui est destiné à l'oxydation catalytique d'une oléfine, d'un alcool t-butylique ou d'un éther méthyl t-butylique en phase vapeur avec un gaz contenant de l'oxygène moléculaire dans le but de produire l'aldéhyde insaturé et l'acide carboxylique correspondants, et qui contient au moins du molybdène, du bismuth et du fer. Le procédé est caractérisé en ce que l'on assèche un mélange en solution ou une bouillie aqueuse contenant les ingrédients du catalyseur, on ajuste la teneur en eau de la matière sèche obtenue de 0,3 à 4 % en poids, et on en fait des pastilles.
PCT/JP2004/013459 2003-12-04 2004-09-15 Procede de production d'un catalyseur destine a la production d'aldehyde insature et d'acide carboxylique insature WO2005053844A1 (fr)

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US11/033,131 US7279442B2 (en) 2003-12-04 2005-01-12 Process for producing catalyst for production of unsaturated aldehyde and unsaturated carboxylic acid

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JP2003-405586 2003-12-04
JP2003405586 2003-12-04

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JP5163273B2 (ja) 2008-05-16 2013-03-13 住友化学株式会社 不飽和アルデヒド及び／又は不飽和カルボン酸製造用触媒の製造方法、並びに不飽和アルデヒド及び／又は不飽和カルボン酸の製造方法

Citations (4)

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JPH06321536A (ja) * 1993-03-09 1994-11-22 Basf Ag 複合金属酸化物組成物
JP2000169149A (ja) * 1998-12-03 2000-06-20 Basf Ag 複合金属酸化物材料、その製造方法、それの使用方法、それを含有する触媒および触媒の使用方法
JP2000237592A (ja) * 1999-02-19 2000-09-05 Mitsubishi Rayon Co Ltd メタクロレインおよびメタクリル酸合成用触媒およびメタクロレインおよびメタクリル酸の製造方法
JP2003251183A (ja) * 2002-02-28 2003-09-09 Nippon Shokubai Co Ltd 不飽和アルデヒド合成用触媒とその製造方法、およびその触媒を用いた不飽和アルデヒドの製造方法

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JPS5898143A (ja) 1981-12-07 1983-06-10 Ube Ind Ltd オレフイン酸化用触媒の製法
DE3930533C1 (fr) 1989-09-13 1991-05-08 Degussa Ag, 6000 Frankfurt, De
JP3251641B2 (ja) 1992-06-19 2002-01-28 三菱レイヨン株式会社 不飽和アルデヒド及び不飽和カルボン酸製造用触媒の製造法
JP3278246B2 (ja) 1993-06-30 2002-04-30 三菱レイヨン株式会社 不飽和アルデヒド及び不飽和カルボン酸合成用触媒の製造法
US6960684B2 (en) * 2002-03-29 2005-11-01 Nippon Shokubai Co., Ltd. Production process for unsaturated aldehyde

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPH06321536A (ja) * 1993-03-09 1994-11-22 Basf Ag 複合金属酸化物組成物
JP2000169149A (ja) * 1998-12-03 2000-06-20 Basf Ag 複合金属酸化物材料、その製造方法、それの使用方法、それを含有する触媒および触媒の使用方法
JP2000237592A (ja) * 1999-02-19 2000-09-05 Mitsubishi Rayon Co Ltd メタクロレインおよびメタクリル酸合成用触媒およびメタクロレインおよびメタクリル酸の製造方法
JP2003251183A (ja) * 2002-02-28 2003-09-09 Nippon Shokubai Co Ltd 不飽和アルデヒド合成用触媒とその製造方法、およびその触媒を用いた不飽和アルデヒドの製造方法

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US20050165253A1 (en) 2005-07-28
US7279442B2 (en) 2007-10-09

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